This invention relates to new chemical compounds, which are of value as antibacterial agents and beta-lactamase inhibitors. More particularly this invention provides certain 2-oxo-1,3-dioxol-4-ylmethyl esters of penicillanic acid 1,1-dioxide (sulbactam).
U.S. Pat. No. 4,234,579 discloses penicillanic acid 1,1-dioxide, and certain esters thereof readily hydrolyzable in vivo, as antibacterial agents and beta-lactamase inhibitors. In particular, U.S. Pat. No. 4,234,579 discloses esters of the formula ##STR1## wherein R.sup.1 is 3-phthalidyl, 4-crotonolactonyl, gamma-butyrolacton-4-yl or a group of the formula ##STR2## wherein R.sup.2 and R.sup.3 are each hydrogen, methyl or ethyl and R.sup.4 is alkyl of 1 to 6 carbons. Said esters of formula I are readily cleaved in vivo to liberate penicillanic acid 1,1-dioxide.
However, it is an object of this invention to provide a new genus of esters of penicillanic acid 1,1-dioxide which hydrolyze readily in vivo to liberate penicillanic acid 1,1-dioxide. Specifically these new esters of penicillanic acid 1,1-dioxide are certain 2-oxo-1,3-dioxol-4-ylmethyl esters.
Certain 2-oxo-1,3-dioxol-4-ylmethyl esters of ampicillin are disclosed in published European patent application No. 39,086.